


The Manly Diary of Dean Winchester

by yaoigirl22



Category: Supernatural
Genre: Dean's Manly Diary, M/M, Spoilers for Season 5-7, Though I think diary out rules manly
Language: English
Status: In-Progress
Published: 2013-01-24
Updated: 2013-05-21
Packaged: 2017-11-26 19:12:41
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 3,003
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/653507
Author URL: https://archiveofourown.org/users/yaoigirl22/pseuds/yaoigirl22
Summary: <blockquote class="userstuff">
              <p>Entry One: I wasn’t sure what shocked me more, that my brother and Angel were together, or that Cas topped.</p>
            </blockquote>





	1. Chapter 1

 

A flutter of wings was his only warning before he found himself lifted and thrown onto the bed, landing with a soft thud, he barely had time to roll over onto his back when lips pressed hard against his, with a moan he opened his mouth and tongue rushed in mapping, **_claiming_**. Hands tugged and pulled at his clothes until they were off, and he laid naked underneath his lover, those same hands roamed over his body making him hot all over, kisses were trailed down his jaw to his neck.

 A mewl escaped his lips when his neck was nip, and licked at his body went limp when his lover sucked on a sensitive spot, lips went lower pulling in a harden bud into a hot wet mouth and suckled on it.

He gasp and arched into the mouth, one of his hands coming up and tangling itself in the short dark soft hair, he moaned his lover’s name when teeth tugged on the nipple.

“Please” he whimpered.

His lover teased his nipple pulling away to play with the other one, going back between the two until they were both sore and red, then a tongue went down licking and nuzzling bare skin sometimes bite hard to leave marks, he whimpered when his legs were lifted and spread, moaning when his inner thighs were nipped, licked and sucked at, sure to leave more marks.

A wet finger pressed at his hole –he had long stop trying figure how his lover was able to lube his fingers so quickly-, he groaned when it slowly pushed in, now sooner did the first finger pull out, a second finger joined it, causing him to moan at the burn that was a mix of pain and pleasure. The two fingers moved in and out of him, brushing against that spot that had him moaning and withering, a third one had him thrusting back against them, until he was begging his lover to fill him.

He gave as soft moan of protest when the fingers pulled out, moaning when his mouth was covered again by his lover, tongue playing with his as his legs were lifted and placed over shoulders. The head of the hard cock pushed inside of him, kept pushing until his lover was deep inside him.

He arched when hips moved, pushing in deep and hard, mouth going to his neck sucking, he mewled, moaned, and gasped as he was brought closer to, his lover pushing in harder  and impossibly deeper, hitting that spot that sent burst of pleasure through him.

“Yes” he moans, crying out when a hand wrapped its way around his throbbing cock, stroking in time with the thrusts until he coming all over the hand, his lover came sometime after groaning softly around the neck he was sucking on.

“Samuel”

Sam opened his eyes, not realizing he had closed them in the first place, and smiled up at Castiel.

“Hi” Sam said.

Castiel gave the faintest of smiles and leaned down to nuzzle the mark he made on Sam’s neck, Sam hummed and titled his head to give the Angel more access, running one hand through short soft hair, the other running down shoulder blades.

Cas gave a soft hum, and kissed the skin, before lifting his head to give butterfly kisses to his human, neither hearing the door click and open.

“Sa—Oh my God!”

Both turned their heads to the door, to see Dean staring at them eyes wide, mouth hanging open.

“Uh, hey Dean” Sam squeaked, his cheeks red with embarrassment.

THUD!

“I believe that could have gone much worse” Castiel said looking at his now unconscious charge.

************

“Here”

Dean lifted his head, he stared at the glass before taking it and downed it, he held it out for more to which Sam gave.

Silence.

Sam was sitting on his bed, the same bed where Cas and his brother…Oh God the imagines!

Sam winced at the soft almost whimper that escaped his brother, the older man had his head bowed, empty glass clenched tightly in his hand. He glanced over at his lover who was seated next to him almost protectively, watching his brother.

“Y-Y-You a-a-a…..” Dean trialed off his voice tight making him squeak.

“Yeah” Sam answered.

“H-H-H-H……”

“Couple of months”

“Five months, two weeks, six days, thirteen hours, twelve minutes, and fifteen seconds” Castiel spoke up, Sam blinked at him, before going to look back at his brother.

 Without lifting his head, Dean held out his glass, Sam filled it and still with his head bowed Dean downed it on one gulp, Sam thought it to be an amazing feat, and he would have said so if he wasn’t worried his brother would lose it.

Silence.

“Dean?”

Dean grunted.

“…You okay?”

Dean blinked, was he okay? Was he okay!?

“No I’m not okay!” he snapped lifting his head.

Both Sam and the Angel tensed.

“Dude I just saw you and Cas GAH!”

The two watched the blonde pace, mumbling to himself, his eye occasionally twitching, neither the Angele or Hunter said anything, just watching the man pace. Finally Dean stopped and turned to them.

“Are you two...you….. know….happy?”

 They both nodded.

“Okay” Dean sighed, then sat down.

“Okay?” Sam asked surprised.

“Okay”

Sam blinked, then “Okay”

Castiel just stared, then decided Humans were just strange before his attention was taken by the television when Dean turned it on, soon Myth Busters kept their attention.

“Soooo” Dean spoke up during a commercial, “who tops?”

“Dean!”

Dean did so enjoy seeing his brother turn red like that.

“I do”

“Cas!”

Dean was pretty sure Castiel got that smug look from him.


	2. Chapter 2

**Summary for the Chapter:**

> Entry 2: Angels Are Cuddle-Sluts.

Now that he was aware of his brother and Angel’s….relationship, Castiel apparently thought it was appropriate to appear whenever he wanted to and **_cuddle_** with his brother Right. In front. Of. Him, and his geeky brother doesn’t even try to stop it!

He didn’t even know Cas liked to cuddle!

He suppose it was just the older brother in him that was annoyed on the fact that Cas was in a relationship with his brother, and no one man, woman, or Angel good enough for his brother to be in a relationship with, one night flings, sure, relationships? They’d have to get through him and his arsenal.

Jessica would probably have been the expectation.   
“Dean?”

Green eyes looked away from where they were glaring at the Angel sitting next to his brother reading a book he had picked up when they went to look up Basilisks at the library.

“What?” he asked.

“You alright?” Sam asked his brother, Castiel looked up from his book, stared at Dean before going back to the book.

“Fine, found anything yet?”

“Nothing, what about you Cas? What did you find?”

 

“That position number twenty-two looks mildly painful”

Both brothers blinked, looked at each other than back at the Angel, both reading the title of the book.

“Cas, are you reading the Kuma Sutra?” Sam asked his lover.

“Yes”

“Why?”

“And why did a public library have it on their shelves?” Dean asked.

“I have heard that it enhances a couple’s sexual experience” Castiel answered, before showing his lover a page in the book, “Sam may we try this one?”

Dean wondered what life would be like with a permanently red-faced brother.

**********

“Seriously?!”

“Hush, Sam is sleeping”

“Yea, in **_my_** bed”

“It was closer”

Dean growled at him and went over to the other bed and after a carful inspection sat down on it, he glanced at the two, who were thankful covered.

He still couldn’t understand how Cas topped when he was the little spoon most of the time.

*********

“Cas?”

“Yes Sam?”

“You’re doing this on purpose aren’t you?”

Cas looked at his lover who was laying his head on his chest, Dean had left sometime later when Cas had appeared and proceed to cuddle with Sam.

“Perhaps” Castiel answered.

Sam snickered, giving an unmanly squeal when he was rolled over onto his back, and a mouth latched onto his neck.

 


	3. Chapter 3

**Summary for the Chapter:**

> Entry 3: I’m pretty sure Angels are not allowed to be possessive, or hold grudges, but it’s not stopping Castiel.

Someone was going to die.

That was what Dean kept thinking over and over again as he watched Cas glare daggers at the woman who was shamelessly flirting with his brother. The Angel even growled- freakin growled! -  when the woman touched Sam’s arm.

And here Dean thought they all could have a nice night of hustling honest men out of their money, what in the world had he been thinking?

While Dean was contemplating when did his life go wrong, Castiel was trying to keep hold of his temper, a feat he was finding hard the more that woman kept flirting  (he’s seen Dean do said flirting enough that he could tell) and touching **_his_** human.

His hand twitched when the woman touched his Sam again, the desire to pull Sam away from the other human and claim him in front of everyone swelled up in him, though Castiel got the impression that Dean wouldn’t take it well.

Blue eyes narrowed when the woman leaned forward, giving Sam an impressive sight of her cleavage, before bringing her mouth closer to his ear, whatever she said made Sam blush, and Castiel’s control snap.

Dean watched in horror as Castiel stood and made his way over to the two humans, the Hunter briefly wondered if he should bring out the Holy Oil

************

 Sam wasn’t sure what happen.

One minute he was talking to Sandy, who admittedly was a bit touchy…and kinky then the next he was being pulled to a warm body and Sandy was looking like the wrath a God had just descended upon her.

And considering how Castiel was growling and glaring at her, Sam wasn’t too far off.

“Um…” Sandy said hesitantly.

“This human is mine” Castiel growled.

In the background Dean groaned.

“But—”

Castiel pulled Sam closer, he suddenly he felt a tug in his stomach and the last thing he heard was his brother yelling “Not in my bed!” before he found himself in their hotel room.

“Cas—!”

Sam yelped his back was nearly slammed into the wall, a hot lips harshly pressed into his, hands ripping off his clothes.

“Cas” Sam gasped against the mouth, hands pushing at the unmoving chest in hopes to get a moment to figure out what was going on. Castiel’s tongue pushed between his lips and mapped out the inside of the human’s mouth, pulling back when Sam started to become light-headed, dipping his head to suck on the curve of Sam’s neck.

“Mine” the Angel growled, biting skin hard enough to leave a mark.

Sam mewled.

Hands grabbed his hips and lifted, and long legs automatically wrapped around a small waist.

The Angel lowered his head located a nipple and suckled,  Sam  moaned, gasping when Castiel’s  clothed cock rubbed against his naked one, he pulled his lover closer, mewling when the thrusting grew faster and harder, until  he was piratical being humped against. He was vaguely aware of Castiel releasing his nipple and nuzzled his neck, his raspy voice growling _“mine, mine, mine, mine”_.

“Cas” Sam whimpered as he came all over the Angel’s clothes.

Several hard thrust later Castiel came as well, the Angel slumping forward, and for some moments there was nothing but soft panting.

“So” Sam said once his voice was able to work again, “care to tell me what that was about?”

Castiel shifted in slight embarrassment for his lack of control over his emotions, but didn’t let his human down or remove he face from Sam’s neck.

“She was touching you” the Angel admitted, and was slightly surprised at how his voice sounded a bit childish.

Sam blinked, then gave a low chuckle when it clicked, he didn’t think Angels could get possessive, not that it mattered, a possessive Castiel was hot.

“Why are you amused?” Castiel asked lifting his head.

“No reason” Sam said, grin on his face, the grin growing when the Angel narrowed his eyes.

“Really it’s nothing, so wanna do a round two in the bed?”

Castiel continued to stare, sure he was being laughed at from some reason, before the thought of more sex won over his suspicion.

“This is Dean’s bed you know” Sam said after he was dumped onto the mattress.

“I am aware” Castiel said as he stripped.

“You know he’s going to pissed”

“I am aware”

“This the fourth time you’ve done this”

“I am aware”

“Should I be worried about this new obsession with having sex in my brother’s bed?”

“I have still not forgiven him taking me to The Den Of Iniquity”

Sam laughed, that laugh turning into a surprised yelp when his legs were lifted and spread.

Some hours later, Dean came back, he took one look at his brother and Angel cuddled up together, his right eye twitched, he then closed the door and went to see if there was another room available.

 

 

 

 

 

 

 


	4. Chapter 4

**Summary for the Chapter:**

> Entry 4: Angels have an amazing stamina….don’t ask me how I know….please don’t ask.

 

It stared at 5pm; Dean had decided to do a night in and turn in early (and get Sam off his back about not getting enough sleep), instead of hitting the nearest bar, he just finished watching Mission Impossible when he heard it. At first he wasn’t sure he heard right, thought it was his imagination, then he heard it again followed by moan and a name.

_“Cas”_

“Oh god!” Dean groaned as the headboard on the other side of the wall banged again, followed by his brother’s whimper. “I got two rooms for a reason!” he then shouted at the wall where it was coming from.

There was silence.

Then the banging resumed in a faster tempo, and  Sam moans and gasp got louder (High pitched even, oooh Dean was so going to tease the hell out of his brother once he was no longer traumatized), Dean was sure the Angel was doing it on purpose.

Fine then, two could play that game.

Now with determination Dean sat down on his bed and turned up volume on the television.

**10pm**

_“Cas, harder, harder, yesss!”_

Dean groaned as he pulled the pillow over his head, trying to muffle out the sounds going on, it didn’t  help, in fact it made it worst.

Dean jumped when there was suddenly his brother let out a loud wail and then silence.

 _“Finally”_ the Hunter thought with a sigh, maybe now he could sleep.

His eyes closed and his breathing started to even.

_“Ah!”_

Dean’s eyes popped open.

**2am**

_“Please, Cas”_

_“Say my name again”_

_“Cas”_

_“Again!”_

_“Castiel!”_

Nine hours, nine freaking hours!

“Damn it Cas!” Dean growled as he banged on the wall, “I’m letting you fuck my brother; the least you could do is let me sleep!”

Sam’s cries got louder, as did the banging, and Dean started looking for the holy oil.

**The next morning.**

Sam came out his room with an obvious limp and refused to look at his older brother though-out breakfast, said older brother who had red tired eyes glared at the smug looking Angel sitting next to Sam.

“Is something wrong Dean?” Castiel asked with that damn smug on his face.

“Yes, there’s a problem!” Dean snapped, “you screwing my brother!”

“Dean!”

“I thought you were fine with Sam and I relationship”

“Not when I can hear it and for NINE hours!”

The two women across them looked at Sam with envy and jealousy, Sam wanted the floor to eat him.

“Angels have very high stamina” Castiel explained.

“No shit!”

“Dean!”

“Sam enjoys it”

“Cas!”

“Um excuse me”

All three eyes looked up, it was the two women from across from them.

“Um we were wondering if you have any straight brothers” One of the girls asked the Angel.


	5. Chapter 5

**Summary for the Chapter:**

> Entry 6: Since when did I become a Couples Counselor?

**Notes for the Chapter:**

> Takes place at the end of S5E17 99 Problems.

 

“Sam is upset with me”

Dean looked over the Angel on the bench, head bowed, hands cradling the bottle of Aspirin he had tossed to him earlier.

“He will not talk to me”

“Well if my boyfriend called me an abomination I wouldn’t speak with him either”

Castiel winced at the reminder of the cruel words he said hours ago, of course at that time they hadn’t sounded cruel.   

“I do not think a mere apology will work” he then said.

“Given the circumstances it actually might”

Dean really didn’t think so, after all there was a reason why alcohol was called the Liquid of Truth and judging from the way Cas was looking, the Angel knew as well.

“Look” Dean then sighed, “Sam is the type of person who’s quick to forgive, not only that but he loves you, and when that kid loves, he loves hard”

Castiel’s shot up, blue eyes wide in surprise, Dean stared back equally surprised.

“Are you serious? But I thought—I mean—you two—”

“I always assumed he merely had…strong feelings for me”

Dean groaned and resisted the urge to smack the Angel upside the hand, then go back into the room and smack his broth as well, instead he took a calming breathe.

“Okay look, Sam loves you and I mean want to make little Sammy hybrids love you”

“I do not think—”

“Shut up I’m talking”

Castiel closed is mouth.

Dean then took another breathe, and continued on, “and I know you love him”

“How—”

“Didn’t I say shut up? Anyway, so I suggest you tell him, apologize and have make-up sex, and not in that order….and not in front of the Priest, don’t think he can handle that, I can barely handle that”

Castiel blinked then stared at him, Dean stared back, use to the staring contest that the Angel seem to enjoy having with him (The Angel did it with his brother too, but he was pretty sure they were having eye-sex, so he’d rather not think about it), then in a flutter of wings the Angel flew off.

Moments later there was a yelp from inside the hotel room. Dean smiled and chuckled, and for a moment everything was back to normal….but only for a moment.

**Notes for the Chapter:**

> Comment are welcomed!

**Author's Note:**

> Comments are welcomed!


End file.
